Pyrrolidine → HCID 11281211, compound

HRID 916668Notes

Reaction equation

HRID 916668 reaction equation
Br[C:2]1[N:10]=[C:9]2[N:4]([CH:5]=[N:6][C:7]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[C:16]3[C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][N:21]=3)=[C:8]2[CH2:11][CH2:12][CH3:13])[N:3]=1.[NH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[F:26][C:25]1[C:20]([C:16]2[N:15]([CH2:14][C:7]3[N:6]=[CH:5][N:4]4[N:3]=[C:2]([N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)[N:10]=[C:9]4[C:8]=3[CH2:11][CH2:12][CH3:13])[CH:19]=[CH:18][N:17]=2)=[N:21][CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 57503314HCID 57503314, compound

Product 1

HCID 11281211HCID 11281211, compound

Procedure

A mixture of 175 (77 mg, 0.185 mmol) and pyrrolidine (0.5 ml) is stirred at room temperature for 4 hours. The solvent is removed in vacuo and the residue is partitioned between water (5 ml) and EtOAc (5 ml). The layers are separated and the aqueous layer is extracted with EtOAc (2×5 ml). The combined extracts are washed with brine (5 ml), dried (Na2SO4) and evaporated. PTLC separation of the residue with 5% MeOH in CH2Cl2 gives the title compound 173 as a white solid. H1 NMR (δ, CDCl3): 8.84 (s, 1H), 8.40 (m, 1H), 7.51–7.56 (m, 1H), 7.21–7.31 (m, 2H), 7.18 (s, 1H), 5.76 (s, 2H), 3.53–3.57 (m, 4H), 2.80–2.84 (m, 2H), 1.99–2.02 (m, 4H), 1.58–1.64 (m, 2H), 0.93 (t, 3H). LC-MS (M+1), 407.10.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is partitioned between water (5 ml) and EtOAc (5 ml)
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (2×5 ml)
  5. washThe combined extracts are washed with brine (5 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPTLC separation of the residue with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-2c17e0b1946547d0b30a910cdf040209
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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